Ep. 4 - Structuring for Success: Tax Strategy and Entity Basics with Chris O'Shell

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Ep. 4 - Structuring for Success: Tax Strategy and Entity Basics with Chris O'Shell

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In this fourth episode of Profits in Practice, host Sarah Webb sits down with Chris O'Shell, CPA and partner at Seamless, to unpack one of the most confusing areas for business owners: legal entity structures and tax strategy. They dive into what "pass-through" really means, how LLCs differ from S corps and partnerships, and why knowing your tax status matters just as much as your legal setup. Chris shares insights on how business owners—especially in professional services like medicine—can pay themselves correctly, avoid costly compliance mistakes, and use entity selection strategically for long-term planning. The conversation also covers retirement planning options, estimated tax payments, and what the latest "Big Beautiful Bill" means for deductions and depreciation. Whether you're launching a new business or refining your structure, this episode is packed with practical, plain-language tax strategy advice.

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